The holiday season is in full swing in Annapolis, with extended shopping hours, live music to shop to, and festive performances. Celebrate the upcoming season with any of the events below and you’re sure to have yourself a merry little Christmas.

Annapolis Entertainment

United States Naval Academy’s Main Chapel hosts a holiday tradition this week, a tradition full of music and holiday cheer. That’s right, it’s the “Holiday by the Bay Concert” on Tuesday, December 11 at 7:30 p.m. The USNA Band is set to perform sing-along songs and lovely holiday songs. The concert exemplifies evern more holiday by offering it free and open to everyone. Celebrate the season with local music. For more information, visit www.usna.edu.

Bay Theatre offers a play called The Foursome until January 3. This fun-loving, friend-filled play features old high school buddies who reunite on the golf course. Enjoy the comedy this week, and invite a few old friends to go! Head to www.baytheatre.org for information about the tickets and showtimes.

The Colonial Players also hosts a play this week: A Christmas Carol. This play/musical is all about the antithesis of the Christmas spirit: Scrooge. However, this Scrooge isn’t the typical one we all know from childhood Christmas movies; rather, Scrooge in The Colonial Players’ rendition gets a mood makeover and takes the crowd on a journey of his redemption. Join in the laughs and heartfelt moments until Sunday, December 16. For tickets and more, look to http://thecolonialplayers.org.

Want more holiday cheer via music? Perhaps “An Annapolis Christmas” at Ram’s Head in downtown Annapolis is up your alley. This Christmas music show features an eclectic mix of local artists and benefits the Annapolis Musicians Fund for Musicians, Inc. There are two chances to catch this show this week: Monday and Tuesday at 7 p.m. Each night costs $30. Thursday, Loudon Wainwright III brings folk to the scene at 8 p.m. for $30. The Rovers, an Irish Celtic rock group, hits the stage with Seamus Keenedy on Friday. The show begins at 8:30 p.m. and costs $22.50. Saturday, indie rockers Bronze Radio Return & Wheeler Brothers play for all ages at noon. Join the light-hearted fun for only $14.50. At 8 p.m. on Saturday, folk musicians by the name of Hard Travelers perform for $25. If jazz/pop music is for you, attend the Rita Coolidge show at 7:30 p.m. This show costs $45. Learn more about these shows on Ram’s Head’s site: http://tickets.ramsheadonstage.com.

49 West Coffeehouse kicks off the week with jazz music from Unified Jazz Ensemble. The show begins at 8 p.m. and costs $6. Wednesday, a few more jazz musicians–Frank & Amy–hit the stage for modern jazz at 8 p.m. The cover charge is $6. Saturday, American Roots Party is in full swing, offering the best of Americana/roots music at 8 p.m. This show collaborative show features a few different performers and costs guests $10 to see. Sunday, it’s back to Jonathan Stone on the guitar for free in the morning and Jenn, Larry & Lumpy at 4 p.m. for free. There are also two new performances scheduled Sunday: Jazz Band Masterclass’ classic jazz at 1 for $10 and Redd Brothers’ Christmas jazz at 7 p.m. for $20. Learn more at www.49westcoffeehouse.com.

Still on the subject of the fast-approaching holidays, Gallery Row in downtown Annapolis plays live music on Thursdays for Christmas shoppers. While this isn’t necessarily an event, the music played is all festive. From five to seven, classic holiday music will be playing; from seven to nine, classical guitar holiday tunes are performed by Ahren Bucheister; and from nine to eleven, saxophone player Jeff Antoniuk plays. Listening is free every Thursday.

Midnight Madness is another means of celebrating and shopping for the Christmas season. This Thursday, December 13, downtown Annapolis businesses are open for extended business hours. Shop, stop at a nice restaurant, and enjoy the downtown spirit.

In West Annapolis, more festivities ensue. On Saturday, December 15, there are screenings of It’s a Wonderful Life, the quintessential Christmas movie, at 10 Annapolis Street from 11 a.m. to 7 p.m. In addition to the screening, there are tons of activities planned for Saturday. First up, a local fire truck visits the streets of West Annapolis from 10:45 to 12:45 a.m. Next, there’s a bake sale at Salon West from 10 to 8 p.m. Students from The Annapolis School of Performing Arts sing Christmas carols from 11 to 2:30. Santa sets up shop at Tara’s Gifts from noon until 4 p.m. The pedicab taxi offers rides from 1 to 5 p.m. There will be singers performing a Madrigale from 2 to 4 p.m. outside. The Giant Peach hosts face painting from 3 to 6 p.m. S’mores can be made around a fire pit outside West Annapolis Antiques from 4 to 5:30 p.m. And lastly, Santa roams around West Annapolis for photo-ops and to gather wish lists from hopeful kids from 4:30 to 8 p.m. For more on these events, head to www.westannapolisbusiness.org.

Celebrating is often best served with a side of luxury. This the philosophy behind Watermark Cruises’ holiday tours by land and water. The Jolly Express Cruise takes participants around the Bay from City Dock until December 31. Decked out with reindeer antlers and a big red nose, this cruise is sure to get you into the holiday spirit! Cruises are scheduled Fridays, Saturdays, and Sundays, but there are a few exceptions. In addition, the hours of operation depend on the day; the tour hours range from 6 to 9 p.m. Tours for adults cost $22 and children cost $12. If you’d like to enjoy the season on land, try out the “Holiday Candelight Stroll” until December 22. This walking tour heads through downtown Annapolis and is led by colonial guides. Tours last one hour. Adults cost $16 and children cost $10. To obtain tickets, head to www.watermarkcruises.com and peruse the calendar.

Annapolis Green

Looking to get involved? Maybe invest in the great outdoors? This Saturday, there’s the chance to get involved in the Trail Monitor Program at Jug Bay Wetlands Sanctuary. This workshop is meant for those who are interested in becoming trail monitors and existing trail monitors. Learn about what being a trail monitor entails from noon to 3 p.m. For more information, head to www.annapolisgreen.com.